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The kind of task is typically sending an email that might rock the boat.

It also applies to purchasing decisions, 'Do I really need this thing?'.

I'll have the idea to send the email (eg suggesting some kind of change), but doing the task involves some social discomfort or risk of blowback.

So what I typically do is put the task on the backlog, and work on everything else, while I let the idea stew - contemplating whether it's a good idea. But this is a form of procrastination or conflict avoidance.

Any suggestions for approaching this kind of situation?

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Do you yet tried to write down the thoughts you made in this decision process? OK, the first email will be a lot of writing. However if you also try to learn something from your decisions, later you will probably spend less time in deciding what to write. – spocchio Nov 20 '13 at 11:08
It sounds like you talk about one specific issue, and that your question is 'How to approach this situation without getting into conflicts'. I suggest you delete the current question and write a new one about the specific issue. As it is now, your question is too broad to give any meaningful answers (Actually, I'm surprised it has not yet received 'close' suggestion for being too broad). – Jan Doggen Nov 22 '13 at 8:20
@JanDoggen - It's fairly general. There's quite a few of these emails. :) It also applies to things like buying things (am I using my money properly?). – dwjohnston Nov 22 '13 at 8:21
up vote 4 down vote accepted

Is it procrastination?

If you're consciously deciding to give the e-mail some thinking time (rather than just putting it off - explained below), I don't think so.

Putting something on the back burner while you "let the idea stew" is a legitimate approach to creativity and decision-making - as long as you give it a bit of active thinking before it does go on the back burner. It's a psychological process called incubation, with lots of research behind it (more info on this relevant Stack Exchange CogSci question, "How is it that taking a break from a problem sometimes allows you to figure out the answer?").

Wikipedia says:

Incubation is defined as a process of unconscious recombination of thought elements that were stimulated through conscious work at one point in time, resulting in novel ideas at some later point in time.

How to stop it turning into procrastination

Of course, it's important not to use incubation as an excuse for all procrastination. If you've consciously made a decision to spend time thinking about something rather than doing it now, spend 10 minutes making some initial notes to get your brain working on the idea. Put an item in your diary (or scheduled in your to-do system) for, say, a couple of days' time to finish the task and pull the trigger (hit send, make the phone call, whatever). By this point you'll probably find you've figured out a lot of a awkwardness of a difficult e-mail, and you can write it much more comfortably, confident that you're not being hasty.

Haven't made your initial notes? Haven't put a date to finish the task in your calendar? That's not incubating, that's procrastinating :-)

I've always liked venture capitalist Fred Wilson's related tip about starting a big project as soon as you can, if only for one hour, so that all the rest of the time you're "getting around to it" your brain is incubating the ideas.

Applying this technique to purchase decisions

You mention your question also applies to decisions like whether to spend money on something - as it happens, I use a similar technique to stop impulse purchases. Fancy buying something, but unsure whether you should? Put it in your calendar for a month's time - if you still need/want it (and can afford it), you can buy it guilt-free, knowing it's not an impulse purchase, and is something that you do actually want, as you've thought about it over a period of time. Nine times out of ten, I find I don't want/need whatever it was any more.

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what does diarised mean? – Manuel Hernandez Nov 22 '13 at 21:06
It means "note an appointment in a diary", but I've just Googled it and realised it's just a word us Brits use...edited for international readers ;-) – Jonathan Deamer Nov 22 '13 at 21:09

All procrastination isn't bad - sometimes putting something "on the back burner" to let your unconscious mind work on it is the most productive thing you can do.

And especially communication that may "rock the boat" is a good category to let sit for a little while. You may find that the issue is not as urgent as you originally felt, or on rereading a draft message you find a less confrontational way to make the same point.

I handle these by adding tasks to my list like "draft response to difficult topic", "edit response to difficult topic", "finalize and send (or not) response to difficult topic", and tickle those to remind me to pay attention to them. The tickle interval depends... I think I've never used less than 4 hours, and generally a day or two is a better idea to help gain perspective. This gives me a couple of opportunities to revise the message I'm going to send to make it as clear and non-inflammatory as possible, or to decide it didn't need to be sent after all.

The same kind of process applies to purchasing, or any other topic - as long as you have ticklers in place to remind you to come back and finalize your decision, this isn't open ended procrastination.

Bonus tip for email: fill in the To: field last. Keep the address in the body of the message to cut and paste later if necessary. This will help prevent you sending an unfinished draft early by accident. (voice of experience, learn from my pain!)

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I would say that in my experience, the feedback is almost always appreciated if presented in the right way. Usually when I feel nervous about sending it it's because I know I'm feeling emotional about how I'm saying it. If you can start out the email with something positive - about the company, the person, the project, etc. and then convey your idea in that context - it will almost always be taken well, or worst case - neutrally.

When I'm feeling uneasy about sending an email like this I usually step back, take a little break, take the emotion out of it and make sure I'm not going to come across as being negative.

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This is one of those areas where you will need to step up and act with courage.

That being said, its nice have a firm foundation upon which you base your courage. There are a couple of things to consider. First, your own principals and second, common goals with others.

Your principals are you set as own standards. Cleanliness, timeliness, quality of production. You own your principals but they are objective. When confronting someone, (rock the boat) you might worry that it might be interpreted as a personal attack. If you make it clear it is about an objective principal you remove that emotional layer at least from your own motives.

Find your common goals. Determine that you do share them. If you don't you need to exit the situation. If you do share them try and be clear that you're in this together, and that you want to move forward.

Finally after considering your principles and common goals. Think about how you would like to be approached about the matter. An email will be saved forever and shared. An email is one sided and impersonal. If this is a serious matter perhaps its best to discuss it in person. More can be said and less can be left up to misinterpretation with a face to face conversation.

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